Methdilazine

Methdilazine (Dilosyn, Tacaryl) is a first-generation antihistamine with anticholinergic properties of the phenothiazine class.

Methdilazine

Clinical data
AHFS/Drugs.com	Monograph
ATC code	R06AD04 (WHO)
Identifiers
IUPAC name 10-[(1-methylpyrrolidin-3-yl) methyl]- 10H-phenothiazine
CAS Number	1982-37-2^Y
PubChem CID	14677
IUPHAR/BPS	7231
DrugBank	DB00902^Y
ChemSpider	14009^Y
UNII	4Q13LY9Z8X
KEGG	D04979^Y
ChEMBL	ChEMBL1200959^N
CompTox Dashboard (EPA)	DTXSID6023282
ECHA InfoCard	100.016.220
Chemical and physical data
Formula	C18H20N2S
Molar mass	296.43 g·mol^−1
3D model (JSmol)	Interactive image
SMILES S2c1ccccc1N(c3c2cccc3)CC4CCN(C)C4
InChI InChI=1S/C18H20N2S/c1-19-11-10-14(12-19)13-20-15-6-2-4-8-17(15)21-18-9-5-3-7-16(18)20/h2-9,14H,10-13H2,1H3^Y Key:HTMIBDQKFHUPSX-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

Synthesis

Methdilazine synthesis:[1] R. F. Feldkamp and Y. H. Wu; Mead Johnson & Company; U.S. Patent 2,945,855 (1960).

See also

• Phenothiazine

References

1. L. W. Marsch and R. Peterson, Arzneimittel Forsch., 9, 715 (1959).

• Rani Basu L, Mazumdar K, Dutta N, Karak P, Dastidar S (2005). "Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine". Microbiol Res. 160 (1): 95–100. doi:10.1016/j.micres.2004.10.002. PMID 15782943.
• Chattopadhyay D, Mukherjee T, Pal P, Saha B, Bhadra R (1998). "Altered membrane permeability as the basis of bactericidal action of methdilazine". J Antimicrob Chemother. 42 (1): 83–6. doi:10.1093/jac/42.1.83. PMID 9700532.
• Chattopadhyay D, Dastidar S, Chakrabarty A (1988). "Antimicrobial properties of methdilazine and its synergism with antibiotics and some chemotherapeutic agents". Arzneimittelforschung. 38 (7): 869–72. PMID 2905130.

The ring-contracted analog, methdilazine shows only very weak activity as a tranquilizer; instead, that agent constitutes an important antihistamine.